Computational study of the synthesis of benzoin derivatives from benzil


Topal K., Unaleroglu C. , Aviyente V.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, cilt.106, ss.1596-1610, 2006 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 106 Konu: 7
  • Basım Tarihi: 2006
  • Doi Numarası: 10.1002/qua.20879
  • Dergi Adı: INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
  • Sayfa Sayıları: ss.1596-1610

Özet

Benzil (1,2-diphenylethane-1,2-dione) undergoes cyanide catalyzed condensation with benzaldehyde to yield O-benzoylated benzoin (2-benzoyl-1,2-diphenylethanone). In this study, the experimentally suggested mechanism has been modeled with PM3 and verified with B3LYP. The effect of the substituent on the reaction yield has been rationalized by considering two benzil derivatives; 1,2-bis(2-chlorophenyl)ethane-1,2-dione and 1,2-bis(2-fluorophenyl)ethane-1,2-dione and three benzaldehyde derivatives; o-fluorobenzaldehyde, o-methylbenzaldehyde and 2-pyridinecarboxaldehyde. The effect of the solvent has been modeled by using the isodensity-surface polarizable continuum (IPCM) model. Reactivity descriptors have been used to justify the reactivity differences of the various substituents.